Basic information
- CAS
103-36-6- Standard SMILES
CCOC(=O)/C=C/c1ccccc1- InChIKey
KBEBGUQPQBELIU-CMDGGOBGSA-N- Molecular formula
- C11H12O2
- Average molar mass
- 176.21 g/mol
- Monoisotopic mass
- 176.08372962
Overview
Ethyl cinnamate is an alkyl cinnamate and an ethyl ester.
Names & identifiers
- Preferred name
- Ethyl Cinnamate
- IUPAC
- ethyl (E)-3-phenylprop-2-enoate
- English name
- Ethyl cinnamate
- Molecular formula
- C11H12O2
- Molecular weight
- 176.21
Names & synonyms
ETHYL CINNAMATE103-36-6EthylcinnamateCinnamic acid ethyl esterEthylcinnamoateethyl (E)-3-phenylprop-2-enoate2-Propenoic acid, 3-phenyl-, ethyl esterEthyl benzylideneacetateFEMA No. 2430SemaSORB 9827C023P3M5JJNSC-6773
Show more names
FEMA 2430EthylphenylacryateEthyl 3-phenylacrylateEthyl 3-phenyl-2-propenoateethyl (2E)-3-phenylprop-2-enoateNSC 6773
DTXCID802520DTXSID9022520RefChem:5810203-104-64192-77-2(E)-ethyl cinnamateEthyl (E)-cinnamateEthyl trans-cinnamate
Database identifiers
- CAS
103-36-6、4192-77-2- PubChem CID
- 637758
- DTXSID
DTXSID601017688- ChEMBL
CHEMBL318196- ChEBI
CHEBI:4895- UNII
- C023P3M5JJ
- EC Number
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 4
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 179
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Esters, Other
CosmeticsUv absorber
FragrancesFragrance Ingredient (Ethyl cinnamate) -> IFRA transparency List
LogP2.91
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.044-1.051
Flavoring AgentsEU Flavoring substances
Solubility
insoluble in water; miscible in alcohols
miscible (in ethanol)
Boiling Point271-272 °C
Vapor Pressure0.00327 [mmHg]
Refractive Index1.558-1.562
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (1623 of 1623) of all reports.
Not Classified
Aggregated GHS information provided per 1623 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: 2-Propenoic acid, 3-phenyl-, ethyl ester
Regulation (EC) No 1831/2003 (amended)
2-Propenoic acid, 3-phenyl-, ethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 3-phenyl-, ethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 28-01-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/16754
Ethyl cinnamate: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 2-Propenoic acid, 3-phenyl-, ethyl ester: Human health tier I assessment
Hazards Summary
Causes somnolence and changes in motor activity in acute inhalation studies of mice; Causes blood changes and effects on enzymes in 17-week intermittent oral studies of rats; [RTECS] Safe when used as a flavoring agent in food; [JECFA] May cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesNot Classified
Safety data
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- wgk
- 1
- tsca
- TSCA listed
- rtecs
Chemistry & industry
Uses & manufacturing
UsesUsed as a fragrance and flavoring agent; [Merck Index] A pine weevil antifeedant. [ChemIDplus]
U.S. Production2020: 405 lb
Consumer UsesFragrance
Household ProductsInformation on 13 consumer products that contain Ethyl Cinnamate in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Cosmetics -> Uv absorber
General Manufacturing Information2-Propenoic acid, 3-phenyl-, ethyl ester: ACTIVE
Applications
DescriptionEthyl cinnamate is the ester of cinnamic acid and ethanol, and is typically found in the essential oil of cinnamon. It is noteworthy that pure ethyl cinnamate has an aroma of cinnamon, complicated by balsamic and red fruit nuances,all of which can be characteristic of a fine Nebbiolo wine's aromatics.
OccurrenceNormally occurring in the trans-form; a cis-form also exists. Reported found in Oriental styrax, in the oil of Campheria galanga and in the rhizomes of Hedychium spicatum. Also reported found in cherry, American cranberry, pineapple, guava, strawberry, fresh blackberry, strawberry jam, soybean, yellow passion fruit juice, hybrid passion fruit juice, apple brandy, quince, prickly pear, strawberry wine, Bourbon vanilla, sea buckthorn, cinnamon leaf and root bark, clove, brandy, rum, sherry, grape wines, cocoa, soybean and other natural sources.
UsesEthyl cinnamate is used in medical intermediate, as a pharmaceutical intermediate and in organic synthesis.
Ethyl cinnamate can be used as a flavoring and fragrance ingredient. It is one of the key odor components reported in Burgundy Pinot noir wines.
Related reactions
111 records
Compound notes
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